Gabe and I Have a Grindr Hookup Contest

Plains, December 2015

The other night I had a couple of free hours, so I went onto a dating app, and I got approached by a hustler!

"I specialize in making older guys feel good," he offered.  "I know it gets lonely when you're over 40, and everyone ignores you."

"Are you kidding?" I exclaimed, annoyed.  "I get approached by younger guys all the time, and I've never yet been turned down! I could hook up with a dozen twinks every night if I wanted to."

 The next day I was complaining about the hustler's chutzpah to my friend Gabe. a recent graduate of the University, now a barista at the gay-friendly coffee house.

"Weren't you exaggerating a bit?" he said.  "I mean, I think you're hot, but most guys my age aren't into anyone over 30, I don't care how much you can bench press."

He paused.  "Now, me, on the other hand, I can attract anyone, any age,  18 to 85.  I just have to bat my eyes and flash my come-hither smile."

I had to admit that Gabe was one of the cutest guys I ever saw: 24 years old, with a nice tight physique and a very thick Kielbasa beneath the belt.  But he was also rather feminine, long-haired, weird red-plastic glasses, with weird plastic bracelets, into poetry readings and art exhibitions and protesting meat processing plants..

"Sure, you can attract androgynous, artsy guys, but what about a man's man?  A guy who drinks beer and goes deer huntin', and wants you to help him skin his kill?"

Gabe, a staunch vegan, whitened.  "Well...I might not want to date him, but I could certainly get him into bed.  Any guy, twink, bear, chubby, Daddy, not a problem."

"Well, I might not want to date a Cute Young Thing who still lives with his parents and has a 10:00 curfew," I countered, "But I could get him into my bed in a second."

"How about we make a little bet?  We each select someone on the app, and the other has to convince him to meet in one hour or less. The loser has to buy the winner dinner."

"What if we both land our guys?"

"Then we have a four-way."

So Saturday night, prime dating and hookup time, we met at my apartment and went to work.

I got to choose someone for Gabe first:

Travis, a 38-year old truck driver from a small town about 50 miles away.  Tall, bearded, hairy, and hung.  His interests actually did include hunting and fishing, as well as football, motorcycles, and "big, chubby guys with some meat on their bones."

The thin, androgynous Gabe was the opposite of what he was looking for!

Gabe gave it his best shot, initiating the conversation with "Want to come over for a beer and a massage?"

I watched their polite, less-than-enthusiastic exchange.

Travis:  "Did you see the game tonight?"

Gabe: [Long pause].  "Uh, no.  I'm here with my friend.  We watched Priscilla, Queen of the Desert.  It's a great old movie about a group of drag queens who get stuck in the Australian outback...."

Travis: [Long pause].  "I'm going hunting next week.  I can't wait."

Gabe:  "[Long pause]. "What music do you like?  I like Owen Pallet, Jay Brannon, a lot of queer indie music."

Travis: [Long pause].  "Um...well, I listen to country-Western, mostly.  I'm going to the Fur Fleet in March.  It's the biggest gathering of bears, cubs, and chubs in the Upper Midwest."

Gabe: Sounds like fun.  I love bears and chubbies."

Travis: [Pointedly] "Me, too."

"That was a dirty trick!" Gabe exclaimed, shutting down the app. "You picked a guy with none of my interests, and I wasn't even his type!"

I shrugged. "All's fair in love and cruising."

"Ok, Mr. Man, now it's my turn."

He picked Bastian, a 18 year old high school senior who was planning to go to art school: long dirty-blond hair, a handsome although rather severe face, a slim physique with an impressive Bratwurst.  Lots of weird plastic bracelets and chains around his neck, two tattoos. Not really my type.

Besides, his profile said "No hookups -- dating and relationships only" and to make matters worse, "My age only."

I glared at Gabe, but said "No problem!  I'll have the hookup arranged in an hour! But leave the room -- I need privacy to work my magic!"

Gabe retreated to the study.  A half hour later, I announced, "Mission accomplished.  Dinner at Chandler's tomorrow night at 7."

How did I get the boy who wasn't into hookups or older guys?

1. Praise.

Boomer: "I just wanted to congratulate you for being out at a young age.  I know it's hard to be gay in the heterosexist high school culture."

Soon I was hearing horror stories about the constant "what girl do you like?" interrogations of his friends, teachers pairing boys and girls together for marriage assignments, parents evoking "when you have a wife and kids" every five minutes.


Boomer: "Have you dated anyone at your school?"

Bastian: "Please! They're too scared to be out."

2. Complaints about Hookups.

Boomer: "Well, there's always this dating app."

Bastian: Are you kidding?  It's full of creepy old guys who just want to get into my pants."

Boomer: "I know.  You can't get rid of them, it's always like 'Come over and do me! I'm more than just a penis!"




3. A Potential Boyfriend

 Boomer: "Hey, I know a guy you might like.  He's 24 years old, single, and completely out."

I told him about Gabe's interest in art, poetry, and queer Indie music, and sent his picture.

Bastian: "Sounds great!  Set us up!"

4. Sealing the Deal

Boomer:  Let me see if he's up for it.  [Pause for a few minutes.]  He says fine.  Dinner tomorrow night at Chandler's.  But the thing is, he's shy, and he won't meet with a new guy unless I'm there as moral support.  Do you mind if there are two of us?"

Bastian: "No problem.  See you both tomorrow.  Can't wait!"

There is more than one way to share a twink.

The story continues with The Hookup Contest, Part 2

See also: The Twink Who Wasn't Interested; Cruising My Host's Son at a Heterosexual Party